Tetrahedron p. 3285 - 3289 (1982)
Update date:2022-08-03
Topics:
Wartski, L.
Bouz, M. El
In order to synthesize γ carbonyl aldehydes which are interesting precursors in organic synthesis, we examine the action of masked acylanions, the lithiated derivatives from 1,3-dithiane 1a and 2-phenyl-1,3-dithiane on selected unsaturated aldehydes: crotonaldehyde 2, cinnamaldehyde 3, 3-methyl butenal 4 and methacrolein 5.In THF 1a leads with the four aldehydes to allylic alcohols.However 1b gives products resulting from C=C and C=O additions.Using THF-HMPA, we show that C=C addition is generally enhanced.Furthermore, in all cases examined C=C and C=O addition take place under kinetic controll: the regioselectivity observed can be interpreted by repulsive interactions due to the substrate and the reagent structure as well as lithium-carbonyl compound interactions.
View MoreTIANJIN NORTH JINHENG CHEMICAL PLANT.
Contact:0086-22-59952083
Address:DongShigu Country In JiXian TianJin China
Penglai Qianwei Chemical Co., Ltd.
Contact:86-535-3357802
Address:Shahelu (north), Penglai, Shandong, China
Shanghai Mio Chemical Co., Ltd
Contact:0086 21- 64401188-622
Address:16 Floor NO.2 Jiefang Building, No. 4855 Dushi Road, 201100 Shanghai, P.R.China
Tianjin Ingenochem Technology Co.,Ltd
Contact:+86-22-23677060
Address:Hitech Green Industry Park K2-9-602, Nankai district
Shenzhen JYMed Technology Co.,Ltd.
website:http://www.jymedtech.com
Contact:+86-755-26612112
Address:1#8,9/F, Biomedicine innovation Industrial Park, No.14, Jinhui Road, Pingshan Sistrict, Shenzhen, China
Doi:10.1039/j39660001519
(1966)Doi:10.1021/jo00314a028
(1981)Doi:10.1016/S0040-4020(01)93782-2
(1976)Doi:10.1055/s-1980-29146
(1980)Doi:10.1039/b404946b
(2004)Doi:10.1080/00397911.2014.970278
(2015)